Alkenyloxy-functional organosilicon compounds, their preparation and use

ABSTRACT

Novel, alkenyloxy-functional organosilicon compounds are described which contain at least one Si-bonded Y radical per molecule having the formula 
     
         --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 
    
      --R 4                                                  (I), 
     in which A represents --O--, --S-- or ##STR1## R 2  represents a linear or branched alkylene radical having from 1 to 7 carbon atom(s) per radical or a cycloalkylene radical having from 5 to 7 carbon atoms per radical, R 3  represents a linear or branched alkylene radical having from 2 to 4 carbon atoms per radical, which may be substituted by a hydroxyl group, methoxy group, ethoxy group or trimethylsiloxy group, R 4  represents a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms(s) per radical, and z is 0, 1, or 2. The alkenyloxy-functional organosilicon compounds are preferably silanes or organopolysiloxanes. The alkenyloxy-functional organopolysiloxanes can be crosslinked, for example, with ultraviolet light. These organopolysiloxanes can also be used for preparing coatings.

The present invention relates to novel, alkenyloxyfunctionalorganosilicon compounds.

BACKGROUND OF THE INVENTION

U.S. Pat. No. 4,617,238 to Crivello et al discloses organopolysiloxanescontaining at least one Si-bonded vinyloxy-functional group per moleculeof the formula

    C.sub.2 C═CH--O--G--

where G represents an alkylene radical or an alkylene radical which isinterrupted by at least one divalent heteroatom or a combination ofheteroatoms. U.S. Pat. No. 4,617,238 describes light-crosslinkablecompositions which contain the abovementioned organopolysiloxanes, andalso onium salts which catalyze the cationic polymerization of theseorganopolysiloxanes.

Therefore, it is an object of the present invention to provideorganosilicon compounds, in particular silanes and organopolysiloxanes,which contain at least one Si-bonded Y radical of formula (I) permolecule. Another object of the present invention is to provideorganosilicon compounds having at least one Si-bonded Y radical offormula (I) which can be prepared from readily available startingmaterials. Still another object of the present invention is to provideorganopolysiloxanes having at least one Si-bonded Y radical of formula(I) per molecule which crosslink rapidly when exposed to light,especially ultraviolet light, during cationic polymerization.

SUMMARY OF THE INVENTION

The foregoing objects and others which will become apparent from thefollowing description are accomplished in accordance with thisinvention, generally speaking, by providing organosilicon compoundswhich contain at least one Si-bonded Y radical per molecule having theformula

    --(CH.sub.2).sub.2 --R.sub.2 --(A--R.sub.3).sub.2 --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I),

in which A represents --O--, --S-- or ##STR2## R² represents a linear orbranched alkylene radical having from 1 to 7 carbon atom(s) per radicalor a cycloalkylene radical having from 5 to 7 carbon atoms per radical,R³ represents a linear or branched alkylene radical having from 2 to 4carbon atoms per radical, which may be substituted by a hydroxyl group,methoxy group, ethoxy group or trimethylsiloxy group, R⁴ represents ahydrogen atom or an alkyl radical having from 1 to 4 carbon atoms(s) perradical, and z is 0, 1 or 2.

The organosilicon compounds according to this invention are preferablysilanes or organopolysiloxanes.

DESCRIPTION OF THE INVENTION

The organosilicon compounds are preferably those of the general formula##EQU1## in which a is 0, 1, 2 or 3, with an average of from 0.0 to 3.0,b is 0, 1, 2 or 3, with an average of from 0.0 to 3.0 and c is 0 or 1,with an average of from 0.01 to 1.0 and the sum of a+b+c is ≦4, with anaverage of from 1.0 to 4.0, R may be the same or different, andrepresents a monovalent substituted or unsubstituted hydrocarbon radicalhaving from 1 to 18 carbon atom(s) per radical, R¹ may be the same ordifferent, and represents a monovalent hydrocarbon radical having from 1to 8 carbon atom(s) per radical which may be interrupted by an etheroxygen atom, and Y is a radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.2 --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I),

in which A represents --O--, --S-- or ##STR3## R² represents a linear orbranched alkylene radical having from 1 to 7 carbon atom(s) per radicalor a cycloalkylene radical having from 5 to 7 carbon atoms per radical,R³ represents a linear or branched alkylene radical having from 2 to 4carbon atoms per radical, which may be substituted by a hydroxyl group,methoxy group, ethoxy group or trimethylsiloxy group, R⁴ represents ahydrogen atom or an alkyl radical having from to 4 carbon atoms(s) perradical, and z is 0, 1 or 2. Preferably these organosilicon compoundshave a molecular weight of preferably from 188 to 300,000 g/mole, andmore preferably a molecular weight of from 232 to 30,000 g/mole.

Preferred organosilicon compounds having at least one Si-bonded Yradical per molecule are silanes of the formula

    R.sub.d YSi(OR.sup.1).sub.3-d

having a viscosity of from 1.5 to 100 mm².s⁻¹ at 25° C., ororganopolysiloxanes of the formula

    Y.sub.c R.sub.3-c SiO(SiR.sub.2 O).sub.n (SiRYO).sub.m SiR.sub.3-c Y.sub.c,

having a viscosity of at least 4 mm².s⁻¹ at 25° C., and more preferablyfrom 4 to 20,000 mm².s⁻¹ at 25° C., where R, R¹, Y and c are the same asabove, d is 0, 1 or 2, n is 0 or an integer of from 1 to 1000 and m is 0or an integer of from 1 to 500.

Examples of radicals represented by R are alkyl radicals, such as themethyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl,tert-butyl, n-pentyl, isopentyl, neo-pentyl or tert-pentyl radicals,hexyl radicals, such as the n-hexyl radical, heptyl radicals, such asthe n-heptyl radical, octyl radicals, such as the n-octyl radical andiso-octyl radicals, such as the 2,2,4-trimethylpentyl radical, nonylradicals, such as the n-nonyl radical, decyl radicals, such as then-decyl radical, dodecyl radicals, such as the n-dodecyl radical,octadecyl radicals, such as the n-octadecyl radical; alkenyl radicals,such as the vinyl and the allyl radicals; cycloalkyl radicals, such asthe cyclopentyl, cyclohexyl, or cycloheptyl radicals andmethylcyclohexyl radicals; aryl radicals, such as the phenyl, naphthyl,anthryl and phenanthryl radicals; alkaryl radicals, such as o-, m-,p-tolyl radicals, xylyl radicals and ethylphenyl radicals; and aralkylradicals, such as the benzyl radical, the α- and the β-phenylethylradicals, with the methyl radical being the preferred radical.

Examples of substituted radicals represented by R are cyanoalkylradicals, such as the β-cyanoethyl radical, and halogenated hydrocarbonradicals, for example, the halogenoalkyl radicals, such as the3,3,3-trifluoro-n-propyl radical, the 2,2,2,2',2',2'-hexafluoroisopropylradical, the hepta fluoroisopropyl radical and halogenoaryl radicals,such as the o-, m-, and p-chlorophenyl radicals.

Examples of radicals represented by R¹ are alkyl radicals, such as themethyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl andtert-butyl radicals. Preferably, the Rl radicals are the methyl andethyl radicals Examples of a hydrocarbon radical represented by R¹ whichis interrupted by at least one ether oxygen atom are the methoxyethyradical and the ethoxyethyl radical. Examples of alkylene radicalsrepresented by R² are those of the formula

    --CH.sub.1 --

    --(CH.sub.2).sub.2 --

    --CH(CH.sub.3)-- and

    --(CH.sub.2).sub.3 --

Examples of cycloalkylene radicals represented by R² are thecyclohexylene radical and the methyl cyclohexylene radical.

Preferably, the R² radical has the formula

    --CH.sub.2 --.

A is preferably oxygen (--O--).

Examples of radicals represented by R³ are those of the formula

    --(CH.sub.2).sub.2 --

    --CH.sub.2).sub.3 --

    --CH.sub.2 CH(CH.sub.3)CH.sub.2 --

    --CH.sub.2 CH(OH)CH.sub.2 --

    --CH.sub.2 CH(OCH.sub.3)CH.sub.2 --

    --CH.sub.2 CH(OC.sub.2 H.sub.5)CH.sub.2 -- and

    --CH.sub.2 CH[OSi(CH.sub.3).sub.3 ]CH.sub.2 --.

Examples of radicals represented by R⁴ are alkyl radicals such as themethyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl andtert-butyl radicals. The R⁴ radical is preferably a hydrogen atom or amethyl radical.

Examples of radicals represented by Y are those of the formula ##STR4##where Z is a hydrogen atom or a radical of the formula --CH₃, --C₂ H₅ or--Si(CH₃)₃.

Examples of preferred Y radicals are those of the formula

    --(CH.sub.2).sub.3 --O--CH═CH--CH.sub.3

    --(CH.sub.2).sub.3 --O--CH.sub.2 --CH.sub.2 --O--CH═CH--CH.sub.3 and

    --(CH.sub.2).sub.3 --O--CH═CH--CH.sub.2 --CH.sub.3,

and more preferably the Y radical has the formula

    --(CH.sub.2).sub.3 --O--CH═CH--CH.sub.3

The invention furthermore relates to a process for the preparation oforganosilicon compounds having at least one Si-bonded Y radical offormula (I) per molecule, which comprises reacting in a lst step anorganic compound (1) of the formula

    H.sub.2 C═CH--R.sup.2 --(A--R.sup.3).sub.z --O13 CH.sub.2 --CH═CH--R.sup.4

in which R², R³, R⁴, A and z are the same as above, with anorganosilicon compound (2) having at least one Si-bonded hydrogen atomin the presence of a catalyst (3) which promotes the addition ofSi-bonded hydrogen to the aliphatic double bond. An organosiliconcompound having at least one Si-bonded Y¹ radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4

(II)

in which R², R³, R⁴, A and z are the same as above, is obtained, andthen in a 2nd step shifting the double bond in the Y¹ radical to thecarbon atom adjacent to the ether oxygen atom by heating theorganosilicon compound having at least one Si-bonded Y¹ radical,obtained in the lst step, in the presence of a catalyst (4) whichpromotes this kind of rearrangement of the double bond. Anyorganosilicon compound having at least one Si-bonded Y radical of theformula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 -R.sup.4                                                  (I),

in which R², R³, R⁴, A and z are the same as above, is obtained.

In order to prepare the organosilicon compounds of this invention, anorganosilicon compound (2) having at least one Si-bonded hydrogen atomis used which is preferably a silane (2a) of the formula

    R.sub.d HSiX.sub.3-d,

in which R and d are the same as above, X may be the same or different,and is a halogen atom, preferably a chlorine atom, or a radical of theformula --OR¹, where R¹ is the same as above, or is anorganopolysiloxane (2b) of the formula

    H.sub.c R.sup.3-c SiO(SiR.sup.2 O).sub.o (SiRHO).sub.p SiR.sup.3-c H.sub.c,

in which R and c are the same as above, o represents 0 or an integer offrom 1 to 1000 and p represents 0 or an integer of from 1 to 500, withthe proviso that at least one Si-bonded hydrogen atom is present permolecule.

Organopolysiloxanes having at least one Si-bonded Y radical of formula(I) per molecule can be prepared from silanes in a modified process inwhich in a lst step an organic compound (1) of the formula

    H.sub.2 C═CH--R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4

in which R², R³, R⁴, A and z are the same as above, is reacted with asilane (2a) having an Si-bonded hydrogen atom of the formula

    R.sub.d HSiX.sub.3-d

in which R, X and d are the same as above, in the presence of a catalyst(3) which promotes the addition of Si-bonded hydrogen to the aliphaticdouble bond, to form a silane having an Si-bonded Y¹ radical of theformula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4                                      (II)

in which R², R³, R⁴, A and z are the same as above, from whichhydrolysis with chloro- or alkoxysilanes and/or condensation withcondensable organopolysiloxanes in a manner known per se subsequentlyproduces an organopolysiloxane having at least one Si-bonded Y¹ radicalof the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH=CH--R.sup.4                                          (III)

in which R², R³, R⁴, A and z are the same as above, and in a 2nd stepthe double bond in the Y¹ radical of the organopolysiloxane is shiftedto the carbon atom adjacent to the ether oxygen atom by heating theorganopolysiloxane having at least one Y¹ radical, obtained in the 1ststep, in the presence of a catalyst (4) which promotes this kind ofrearrangement of the double bond, and thereafter an organopolysiloxanehaving

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I)

in which R², R³, R⁴, A and z are the same as above, is obtained.

The organic compounds (1) are preferably used in the addition reactioncarried out in the lst step of the process according to the invention inamounts such that at least 1 mole, preferably at least 1.5 moles, oforganic compound (1) is present per gram-atom of Si-bonded hydrogen inthe organosilicon compound (2). If R⁴ in the organic compound (1) ishydrogen, preferably the organic compound (1) is used in an amount suchthat 4 to 8 moles of organic compound are present per gram-atom ofSi-bonded hydrogen in the organosilicon compound (2). This excess oforganic compound (1) ensures that the addition does not take place atboth terminal aliphatic double bonds but at only one in each case, andthus diaddition is suppressed.

Examples of organic compounds (1) which are used in the additionreaction which occurs in the lst step of the process according to thisinvention are those of the formula ##STR5## where Z represents ahydrogen atom or a radical of the formula --CH₃, --C₂ H₅ or --Si(CH₃)₃.

Preferred organic compounds (1) employed in the process of thisinvention are diallyl ether, ethylene glycol bis(allyl ether) and allylbut-2-enyl ether, and more preferably a diallyl ether is employed.

The organic compounds (1) are readily obtainable, as shown by thefollowing exemplary reactions, which take place under basic conditionsand phase transfer catalysis: ##STR6##

Processes for their preparation are, for example, described in H. H.Freedman and R. A. Dubois, Tetrahedron Letters No. 38, page 3251 to3254, 1975; Houben-Weyl, Methoden der organischen Chemie, volume VI/3,page 24 to 32, 1965; and GB-A 913,919.

Catalysts (3) promoting the addition of Si-bonded hydrogen to thealiphatic double bond which are used in the process of this inventionmay also be the same catalysts which heretofore could have been used topromote the addition of Si-bonded hydrogen to aliphatic double bonds.Catalyst (3) is preferably a metal from the group of platinum metals ora compound or complex from the group of platinum metals. Examples ofcatalysts of this type are metallic and finely divided platinum, whichcan be supported on carriers, such as silicon dioxide, aluminum oxide oractivated carbon, compounds or complexes of platinum, such as platinumhalides, for example PtCl₄, H₂ PtCl₆.6 H₂ O, Na₂ PtCl₄.4 H₂ O,platinumolefin complexes, platinum-alcohol complexes, platinumalcoholate complexes, platinum ether complexes, platinum aldehydecomplexes, platinum ketone complexes, including reaction products of H₂PtCl₆.6 H₂ O and cyclohexanone, platinum-vinyl siloxane complexes, suchas platinum, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complexes with orwithout detectable inorganically-bound halogen,bis(gammapicoline)platinum dichloride, trimethylene dipyridine platinumdichloride, dicyclopentadiene platinum dichloride, dimethylsulfoxideethylene platinum(II) dichloride and also reaction products of platinumtetrachloride with an olefin and a primary amine or a secondary amine ora primary and a secondary amine according to U.S. Pat. No. 4,292,434 toLindner et al, such as the reaction product from platinum tetrachloridedissolved in 1-octene with sec-butylamine or ammonium platinum complexesaccording to EP-B 110,370.

Catalyst (3) is preferably used in an amount of from 0.1 to 10,000 ppm(parts by weight per million parts by weight), and more preferably in anamount of from 10 to 100 ppm, calculated as the elemental metal, fromthe group of platinum metals and based on the total weight of organiccompound (2) having at least one Si-bonded hydrogen atom.

The addition reaction (or hydrosilylation reaction) in the 1st step ofthe process according to this invention is preferably carried out atatmospheric pressure, i.e., at about 1020 hPa (abs.), but it may also becarried out at higher or lower pressures. Furthermore, the additionreaction is preferably carried out at a temperature of from 40° to 200°C., and more preferably from 70° to l40° C.

The hydrosilylation carried out in the lst step of the process of thisinvention produces organosilicon compounds having at least one Si-bondedY¹ radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4                                      (II)

in which R², R³, R⁴, A and z are the same as above. Excess organiccompound (1) is removed from the organosilicon compound having at leastone Si-bonded Y¹ radical by distillation.

The silanes having an Si-bonded Y¹ radical of formula (II) which areobtained in the lst step of the process of this invention can be reactedby mixed hydrolysis with chloro- or alkoxy-silanes and/or bycondensation with condensable organopolysiloxanes in a manner known perse to form organopolysiloxanes having at least one Si-bonded Y¹ radicalof formula (II) per molecule.

Preferably, chloro- or alkoxy-silanes of the formula

    ReSiX.sub.4-e ,

are used, in which R is the same as above, X is the same or different,and is a chlorine atom or a radical of the formula --OR¹, where R¹ isthe same as above, and e is 0, 1, 2 or 3.

Preferably, condensable organopolysiloxanes of the formula

    HOR.sub.2 SiO(SiR.sub.2 O).sub.q H,

as used, in which R is the same as above and q is an integer having avalue of at least 1, or linear, condensable organopolysiloxanes obtainedfrom cyclic organopolysiloxanes of the formula

    (SiR.sub.2 O).sub.r,

in which R is the same as above and r is an integer having a value offrom 3 to 10, by condensation and/or equilibration in a manner known perse.

The catalysts (4) used to promote the shift of the double bond in the Y¹radical of formula (II) to the carbon atom adjacent to the ether oxygenin the 2nd step of the process according to this invention may be thesame catalysts which have been or could have been used heretofore topromote this kind of rearrangement of the double bond. Examples ofcatalysts (4) are metallic or finely divided platinum, ruthenium,rhodium and palladium, in which these metals may be supported oncarriers such as activated carbon, and compounds or complexes of theseelements, which are soluble in the organosilicon compound having atleast one Si-bonded radical Y¹ of formula (II) or which are fixed tocarriers such as activated carbon or polymeric phosphine ligands.Examples of preferred catalysts (4) are those of the formula RuCl₂(PPh₃)₃, RuHCl(PPh₃)₃, RuHCl(CO)(PPh₃)₃, RuH₂ (CO)(PPh₃)₃ and RuH₂(PPh₃)₄.

The catalyst (4) is preferably used in an amount of from 0.1 to 1000 mg,preferably from 1 to 50 mg, calculated in each case as the elementalmetal, per gram-mole of Sibonded Y¹ radical in the organosiliconcompound having at least one Si-bonded Y¹ radical of formula (II) whichis obtained in the 1st step of the process of this invention.

In order to shift the double bond to the carbon atom adjacent to theether oxygen atom in the Y¹ radical of formula (II), the organosiliconcompound having at least one Si-bonded Y¹ radical of formula (II)obtained from the 1st step of the process of this invention is mixedwith catalyst (4) and the mixture is heated. The reaction is preferablycarried out at a temperature of from 80 to 200.C, and more preferablyfrom 100 to l50.C, preferably at atmospheric pressure, i.e., at about1020 hPa (abs.), and preferably over a period of from 2 to 20 hours andmore preferably from 4 to 10 hours. It is preferred that the reaction beconducted in the absence of a solvent.

The organosilicon compound having at least one Si-bonded Y radical offormula (I) which is obtained in the 2nd step of the proces of thisinvention is a mixture of cis-/trans-isomers in respect of the radicalY, the cisisomer usually predominating. If, for example, Y is a1propenyloxypropyl radical, the following mixture of isomers is present:##STR7##

Finally, it is also possible to prepare the organosilicon compounds ofthis invention having at least one Si-bonded Y radical of formula (I) byreacting an organic compound of the formula

    H.sub.2 C═CH--R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4,

in which R², R³, R⁴, A and z are the same as above, with anorganosilicon compound (2) having at least one Si-bonded hydrogen atomin the presence of a catalyst (3) which promotes the addition ofSi-bonded hydrogen to the aliphatic double bond.

The organopolysiloxanes prepared according to the invention having atleast one Si-bonded Y radical of formula (I) are crosslinkable bylight-initiated cationic polymerization. Catalysts used for thelight-initiated crosslinking may, for example, be thebis(dodecylphenyl)-iodonium salts described in U.S. Pat. No. 4,279,717to Eckberg et al, such as bis(dodecylphenyl)iodoniumhexafluoroantimonate or bis(dodecylphenyl)iodoniumhexafluoroarsenate.

The invention therefore relates to the use of organopolysiloxanes havingat least one Si-bonded Y radical per molecule, in which Y is the same asabove, in light-crosslinkable compositions based on previously mentionedorganopolysiloxanes.

The organopolysiloxanes according to this invention having at least oneSi-bonded Y radical of formula (I) are preferably crosslinked byultraviolet light, preference being given to that having a wavelength inthe range of from 200 to 400 nm. The ultraviolet light can be generated,for example, in xenon lamps, low pressure mercury lamps, medium pressuremercury lamps or high pressure mercury lamps. Light-crosslinking is alsopossible using light with a wavelength of from 400 to 600 nm, i.e.,so-called "halogen light". The organopolysiloxanes according to thisinvention having at least one Si-bonded Y radical of formula (I) can becrosslinked using light in the visible range if commercially availablephotosensitizers are concomitantly used.

Finally, the invention also relates to the use of theorganopolysiloxanes of this invention having at least one Si-bonded Yradical, in which Y is the same as above, in the preparation oflight-crosslinkable coatings.

Examples of surfaces to which the coatings of this invention can beapplied are those of paper, wood, cork, plastic films, for example,polyethylene films or polypropylene films, ceramic objects, glass,including glass fibers, metals, boards, including those made ofasbestos, and of woven and nonwoven cloth made from natural or syntheticorganic fibers.

The application of the organopolysiloxanes of this invention having atleast one Si-bonded Y radical of formula (I) to the surfaces which areto be coated can be carried out using any suitable and widely knownmethod for producing coatings from liquid substances, for example, bydip coating, brush coating, casting, spray coating, roller coating,printing for example, using an offset gravure roll coater, knife coatingor draw bar coating.

EXAMPLE 1

(a) About 28 g of trimethylbenzylammonium chloride (0.1 mole) are addedto a solution containing 600 g of NaOH (15 moles) in 600 ml of water.About 290 g of allyl alcohol (5.0 moles) and 425 g of allyl chloride(5.5 moles) are then added to this mixture. The reaction mixture isheated for eight hours at 40° to 60° C. The resulting sodium chlorideprecipitate is then substantially dissolved in water. The organic phaseis separated off and dried using sodium sulfate. Distillation through ashort vigreux column at 92 to 94° C. produces 415 g of diallyl ether (85percent of theory).

(b) About 294 g of diallyl ether, prepared in accordance with (a) above,is initially introduced into a three-necked flask fitted with aninternal thermometer and reflux condenser, together with 0.5 ml of asolution of platinum tetrachloride in 1-octene, containing 20 mg ofplatinum, calculated as the element, and the mixture is heated to refluxtemperature. About 118 g of methylhydrogendiethoxysilane is then addeddropwise to this mixture over a period of two hours, the temperature ofthe vapor space remaining between 86° and 91° C. The reaction mixture isallowed to react at this temperature for an additional two hours, thenthe excess of diallyl ether is distilled off using a short packed columnand 125 g of pure (allyloxypropyl)methyldiethoxysilane are obtained byfractional distillation through a vigreux column at 40° to 42° C. and 3hPa (abs.).

(c) About 200 ppm (based on the total weight of the silane used) oftris(triphenylphosphine)ruthenium(II) dichloride are added to 125 g ofthe (allyloxypropyl)methyldiethoxysilane described in (b) above. Afterheating for four hours at 150° C. (95 percent conversion),(1-propenyloxypropyl)methyldiethoxysilane of the formula ##STR8## isobtained, which is present as a mixture of cis-/transisomers. Thefollowing ¹ H-NMR spectrum is obtained from the product:

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=0.12 ppm (s, 3H, Si--CH₃),

(40 mol-%) 0.65 ppm (m, 2,Si--CH₂ --),

1.22 ppm (t, 6H, Si--O--CH₂ --CH₃),

1.54 ppm (dd, 3H, CH₃ --CH═),

1.70 ppm (m, 2H, Si--CH₂ --CH₂ --),

3.59 ppm (t, 2H, -O--CH₂ --CH₂),

3 76 ppm (q, 4H, Si--O--CH₂ --),

4.75 ppm (dq, 1H, CH₃ --CH=),

6.19 ppm (dq, 1H, =CH--O--).

cis-isomer

(60 mole-%) δ=0.13 ppm (s, 3H, SiCH₃),

0.65 ppm (m, 2H, Si--CH₂ --),

1.22 ppm (t, 6H, Si--O--CH₂ --CH--),

1.58 ppm (dd, 3H, CH₃ --CH═),

1.70 ppm (m, 2H, Si--CH₂ --CH₂ --),

3.69 ppm (t, 2H, --O--CH₂ --CH₂ --),

3.77 ppm (q, 4H, Si--O--CH₂ --),

4.36 ppm (dq, 1H, CH₃ --CH═),

5.92 ppm (dq, 1H, ═CH--O--).

EXAMPLE 2

(a) About 70 g of the (allyloxypropyl)methyldiethoxysilane described inExample l(b) above are mixed with g of trimethylethoxysilane and 15 g ofwater and 2 g of a strongly acid ion exchange medium for six hours at80° C. The reaction mixture is then filtered and evaporated in vacuo (5hPa). The residue remaining is 50 g of product, having a viscosity of 15mm² s and a ratio of Si-bonded allyloxypropyl radical to Si-bondedmethyl radical of 1:2.33, which corresponds to a siloxane of the averagecomposition.

    (CH.sub.3).sub.3 SiO[CH.sub.3 Si(C.sub.3 H.sub.6 OCH.sub.2 CH═CH.sub.2)O].sub.4.5 Si(CH.sub.3).sub.3.

In order to remove traces of acid, the siloxane obtained in this manneris stirred for 15 hours with MgO in amounts of 5 percent by weight,based on the total weight of siloxane, and then the mixture is filtered.(b) About 200 ppm (based on the total weight of siloxane) oftris(triphenylphosphine)ruthenium(II) dichloride are added to 50 g ofthe siloxane described in (a) above. After heating for eight hours atl30° C., a siloxane is

    (CH.sub.3).sub.3 SiO[CH.sub.3 Si(C.sub.3 H.sub.6 OCH═CH--CH.sub.3)O].sub.4.5 Si(CH.sub.3).sub.3

and a ratio of cis-isomer to trans-isomer of 2:1 and with the following¹ H-NMR spectrum:

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=4.77 ppm (dq, 1H, CH₃ --CH═), 6.18 ppm (dq, 1H,═CH--O--).

cis-isomer δ=4.35 ppm (dq, 1H, CH₃ --CH═), 5.92 ppm (dq, 1H, ═CH--O--).

EXAMPLE 3

(a) The method described in Example 1(b) above is repeated, except that101 g of methylhydrogendiethoxysilane are used instead of 118 g ofmethylhydrogendiethoxysilane. Fractional distillation at 80° to 85° C.and 7 hPa (abs.) is used to produce (allyloxypropyl)methyldichlorosilanein 70 percent yield.

(b) About 520 g of a mixture of cyclic dimethylpolysiloxanes having 3 to7 siloxane units per molecule are stirred for two days with 62.4 g ofKOH at 120° C., in which the water formed during the reaction isremoved. The linear potassium siloxanolate thus obtained is diluted with300 g of toluene and cooled to +10° C. To this solution are then addeddropwise, so that the temperature of the reaction mixture does notexceed 20° C., 96 g of (allyloxypropyl)methyldichlorosilane, which hasbeen prepared in accordance with (a) above, and a solution of 11 g oftrimethylchlorosilane in 100 g of toluene. After the reaction mixturehas reacted for an additional one hour at room temperature, 300 ml ofwater are added t the reaction mixture and the reaction mixture isstirred until two clear phases have been formed. The aqueous phase isremoved and the organic phase is freed from traces of acid using sodiumbicarbonate solution. This solution is then dried by azeotropicdistillation, and a diorganopolysiloxane blocked in the terminalpositions with trimethylsiloxy groups and composed of dimethylsiloxaneunits and (allyloxypropyl)methylsiloxane units having an average ratioof Si-bonded allyloxypropyl radicals to Si-bonded methyl radicals of0.028 and a viscosity of about 100 mm².s at 25° C. is obtained bysubsequent evaporation in vacuo at 5 hPa (abs.).

(c) About 200 ppm (based on the total weight of thediorganopolysiloxane) of tris(triphenylphosphine)ruthenium(II)dichloride are added to 50 g of the diorganopolysiloxane obtained in (b)above. After eight hours at 130° C., a diorganopolysiloxane having aviscosity of about 230 mm².s at 25° C. is obtained, in which theallyloxypropyl radicals have almost quantitatively been rearranged into1-propenyloxypropyl radicals. The ratio of trans-isomers to cisisomersis 35:65. The following ¹ H-NMR spectrum is obtained:

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=4.7 ppm (1H, CH₃ --CH═), 6.1 ppm (1H, ═CH--O--).

cis-isomer: δ=4.3 ppm (1H, CH₃ --CH═), 5.8 ppm (1H, ═CH--O--).

EXAMPLE 4

(a) Ethylene glycol bis(allyl ether) is obtained by reacting allylchloride with ethylene glycol in an analogous procedure to that used inthe preparation of diallyl ether in accordance with Example l(a) above.

(b) About 1.5 ml of a solution of platinum tetrachloride in 1-octene,containing 60 mg of platinum, calculated as the element, are added to142 g of ethylene glycol bis(allyl ether). The mixture is heated tol30.C, then 69 g of a dimethylpolysiloxane having dimethylhydrogensiloxygroups as terminal units and an average molecular weight of 690 g/moleare added dropwise. After conversion of more than 99 percent of allSi-bonded hydrogen atoms in the dimethylpolysiloxane, all componentswhich are volatile at 100° C. and at 5 hPa (abs.) are removed bydistillation. A clear dimethylpolysiloxane product is obtained, havingterminal units of the formula

    CH.sub.2 ═CHCH.sub.2 OCH.sub.2 CH.sub.2 O(CH.sub.2).sub.3 (CH.sub.3).sub.2 SiO1/2

and an average ratio of Si-bonded allyloxyethyloxypropyl radicals toSi-bonded methyl radicals of 0.104, and a viscosity of 13.8 mm².s at 25°C.

(c) About 200 ppm (based on the total weight of dimethylpolysiloxane) ofRuHCl(PPh3)₃ are added to 50 g of the dimethylpolysiloxane obtained in(b) above. After heating for eight hours at 130° C., adimethylpolysiloxane having a viscosity of 23.4 mm².s is obtained, whoseallyloxy-ethyloxypropyl groups have almost completely (97 percentconversion according to the ¹ HNMR spectrum) been rearranged to form1-propenyloxyethyloxypropyl groups. The ratio of trans-isomers tocis-isomers is 26:74.

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=4.79 ppm (dq, 1H, CH₃ --CH═), 6.26 ppm (dq, 1H,═CH--O--).

cis-isomer: δ=4.40 ppm (dq, 1H, CH₃ --CH═), 5.98 ppm (dq, 1H, =CH--O--).

EXAMPLE 5

(a) Allyl but-2-enyl ether is obtained by reacting but-2-en-l-ol withallyl chloride in an analogous procedure to that used in the preparationof diallyl ether in accordance with Example l(a) above.

(b) About 84 g of allyl but-2-enyl ether are heated under reflux (about120° C.) in a three-necked flask fitted with a reflux condenser, stirrerand dropping funnel. To this are added dropwise over a period of twohours a solution containing 82 g of triethoxysilane, in which 2 mg ofplatinum, calculated as the element, are dissolved in the form of asolution of platinum tetrachloride in 1-octene. After heating for anadditional five hours under reflux, more than 99 percent of theSi-bonded hydrogen atoms have been converted. The intermediate obtainedin this manner, (but-2-enyloxypropyl)triethoxysilane, is purified bydistillation at C and at 7 hPa (abs.) and contains 5 percent by weight,based on the total weight of the intermediate, of(but-1-enyloxypropyl)triethoxysilane.

(c) About 200 ppm (based on the total weight of intermediate) oftris(triphenylphosphine)ruthenium(II) dichloride are added to 50 g ofthe intermediate obtained in (b) above. After heating for eight hours at130 C, the (butenyloxypropyl)triethoxysilane is obtained in a yield of70 percent. The ratio of trans-isomers to cis-isomers is 35:65. Theproduct gives the following lH-NMR spectrum:

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=0.63 ppm (m, 2H, Si--CH₂ --),

0.93 ppm (t, 3H, CH₃ --CH₂ --CH═),

1.19 ppm (t, 9H, Si--O--CH₂ --CH₃),

1.70 ppm (m, 2H, Si--CH₂ --CH₂ --),

1.89 ppm (ddq, 2H, CH₃ --C₂ --CH═);

3.55 ppm (t, 2H, --O--CH₂ --CH₂ --),

3.76 ppm (q, 6H, Si--O--CH₂ --),

4.72 ppm (dt, 1H, CH₃ --CH₂ --CH═CH--),

6.14 ppm (dt, 1H, CH₃ --CH₂ --CH═CH--).

cis-isomer: δ=0.63 ppm (m, 2H, Si--CH₂ --),

0.92 ppm (t, 3H, CH₃ --CH₂ --CH═),

1.19 ppm (t, 9H, CH₃ --CH₂ --CH₃)

1.70 ppm (m, 2H, Si--CH₂ --CH₂ --),

2.04 ppm (ddq, 2H, CH₃ --CH₂ --CH═);

3.63 ppm (t, 2H, --O--CH₃ --CH₂ --),

3.76 ppm (q, 6H, Si--O--CH₂ --),

4.25 ppm (dt, 1H, CH₃ --CH₂ --CH═CH),

5.81 ppm (dt, 1H, CH₃ --CH₂ --CH═CH--).

EXAMPLE 6

(a) About 240 g of a diorganopolysiloxane having terminaltrimethylsiloxy groups and composed of methylhydrogensiloxane units anddimethylsiloxane units, having 0.08 percent by weight of Si-bondedhydrogen and an average chain length of 80, are heated under reflux with120 g of diallyl ether and 0.2 g of a solution of platinum tetrachloridein 1-octene which contains 8 mg of platinum, calculated as the element,until the amount of Si-bonded hydrogen used has been reduced to 2percent. The excess of diallyl ether is distilled off at 60° C. and at 5hPa (abs.). The intermediate obtained is a diorganopolysiloxane havingterminal trimethylsiloxy groups and is composed ofmethyl(allyloxypropyl)siloxane units and dimethylsiloxane units, and hasa viscosity of 460 mm².s at 25° C.

(b) About 200 ppm (based on the total weight of intermediate) ofRuHCl(PPh₃)₃ are added to 50 g of the interintermed mediate obtained in(a) above. After heating for eight hours at 130° C., the productobtained is a diorganopolysiloxane having terminal trimethylsiloxygroups and composed of methyl(l-propenyloxypropyl)siloxane units anddimethylsiloxane units. The ratio of trans-isomers to cis-isomers is34:66. The product gives the following ¹ H-NMR spectrum:

¹ H-NMR spectrum (CDCl₃):

trans-isomer: δ=4.7 ppm (1H, CH₃ --CH═), 6.2 ppm (1H, ═CH--O--).

cis-isomer: δ=4.3 ppm (1H, CH₃ --CH═), 5.9 ppm (1H, ═CH--O--).

EXAMPLE 7

About 2 g of a 50 percent solution of bis(dodecylphenyl)iodoniumhexafluoroantimonate, which has been prepared according to U.S. Pat. No.4,279,717 in propenylene carbonate are added to 50 g of the productprepared in Example 6. The mixture is applied with a doctor blade to apolyethylene film to a thickness of 100 μ. Two medium pressure mercurylamps with an output of 80 watt/cm of tube length are arranged at adistance of 10 cm from the coated polyethylene film. After exposure toUV light for two seconds, a tackfree coating is obtained.

What is claimed is:
 1. An organosilicon compound comprising units of thegeneral formula ##EQU2## in which R is selected from the groupconsisting of a monovalent unsubstituted hydrocarbon radical having form1 to 18 carbon atom(s) per radical and a monovalent substitutedhydrocarbon radical having from 1 to0 18 carbon atom(s) per radical, R¹is selected from the group consisitng of a monovalent hydrocarbonradical having from 1 to 8 carbon atom(s) per radical and a monovalenthydrocarbon radical having from 1 to 8 carbon atom(s) per radical whichis interrupted by an ether oxygen atom, and Y is a radical of theformula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4                                      (I)

in which A is selected from the group consisting of --O--, --S-- and##STR9## R² is selected from the group consisting of an alkylene radicalhaving from 1 to 7 carbon atoms(s) per radical and a cycloalkyleneradical having from 5 to 7 carbon atoms per radical, R³ is selected fromthe group consisting of an alkylene radical having form 2 to 4 carbonatoms per radical and an alkylene radical having from 2 to 4 carbonatoms per radical which is substituted with a group selected from thegroup consisting of a hydroxyl group, methoxy group, ethoxy group and atrimethylsiloxy group, R⁴ is selected from the group consisting of ahydrogen atom and an alkyl radical having from 1 to 4 carbon atoms(s)per radical, with the proviso that the organosilicon compound containsat least one Si-bonded Y radical per molecule, a is 0, 1, 2 or 3, b is0, 1, 2 or 3 and c is 0 or 1, and the sum of a+b+c is ≦4 and z is 0, 1or
 2. 2. The compound of claim 1, wherein the organo-silicon compound isa silane.
 3. The compound of claim 2, wherein the organosilicon compoundis a silane of the formula

    R.sub.d YSi(OR.sup.1).sub.3-d

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having form 1 to 18 carbon atom(s) perradical and a monovalent substituted hydrocarbon radical having from 1to0 18 carbon atom(s) per radical, R¹ is selected from the groupconsisitng of a monovalent hydrocarbon radical having from 1 to 8 carbonatom(s) per radical and a monovalent hydrocarbon radical having from 1to 8 carbon atom(s) per radical which is interrupted by an ether oxygenatom, and Y is a radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4                                      (I)

in which A is selected from the group consisting of --O--, --S-- and##STR10## R² is selected from the group consisting of an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radicla, R³ isselected from the group consisting of an alkylene radical having form 2to 4 carbon atoms per radical and an alkylene radical having from 2 to 4carbon atoms per radical which is substituted with a group selected fromthe group consisting of a hydroxyl grup, methoxy group, ethoxy group anda trimethylsiloxy group, R⁴ is selected from the group consisting of ahydrogen atom and an alkyl radical having from 1 to 4 carbon atoms(s)per radical, d is 0, 1 or 2 and z is 0, 1 or
 2. 4. The compound of claim1, wherein the organosilicon compound is an organopolysiloxane.
 5. Thecompound of claim 4, wherein the organosilicon compound is anorganopolysiloxane of the formula

    Y.sub.c R.sup.3-c SiO(SiR.sub.2 O).sub.n (SiRYO).sub.m SiR.sub.3-c Y.sub.c

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atom(s) perradical and a monovalent substituted hydrocarbon radical having from 1to 18 carbon atom(s) per radical, c is 0 or 1, n is 0 or an integer offrom 1 to 1000, m is 0 or an integer of from 1 to 500 and Y is a radicalof the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I)

with the proviso that at least one Y radical is present per molecule, inwhich A is selected from the group consisting of --O--,--S--, and##STR11## R² is selected from the group consisting of an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radical, R³ isselected from the group consisting of an alkylene radical having from 2to 4 carbon atoms per radical and an alkylene radical having from 2 to 4carbon atoms per radical which is substituted with a group selected fromthe group consisting of a hydroxyl group, methoxy group, ethoxy groupand a trimethylsiloxy group, R⁴ is selected from the group consisting ofa hydrogen atom and an alkyl radical having from 1 to 4 carbon atom(s)per radical and z is 0, 1 or
 2. 6. A composition containing theorganosilicon compound of cliam 4 which crosslinks on exposure to lighthaving a wave length of from 200 to 600 nm.
 7. The compound of claim 1,wherein the organosilicon compound is a silane of the formula

    R.sub.d YSi(OR.sup.1).sub.3-d

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atom(s) perradical and a monovalent substituted hydrocarbon radical having from 1to 18 carbon atom(s) per radical, R¹ is selected from the roupconsisting of a monovalent hydrocarbon radical having from 1 to 8 carbonatom(s) per radical and a monovalent hydrocarbon radical having from 1to 8 carbon atom(s) per radical which is interrupted by an ether oxygenatom, and Y is a radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I)

in which A is selected from the group conisisting of --O--,--S-- and##STR12## R² is selected from the group consisting of an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radical, R³ isselected from the group consisting of an alkylene radical having from 2to 4 carbon atoms per radical and an alkylene radical having from 2 to 4carbon atoms per radical which is substituted with a group selected fromthe group consisting of a hydroxyl group, methoxy group, ethoxy groupand a trimethylsiloxy group, R⁴ is selected from the group consisting ofa hydrogen atom and an alkyl radical having from 1 to 4 carbon atom(s)per radical, d is 0, 1 or 2 and z is 0, 1 or
 2. 8. The compound of claim1, wherein the organosilicon compound is an organopolysiloxane of theformula

    Y.sub.c R.sup.3-c SiO(SiR.sub.2 O).sub.n (SiRYO).sub.m SiR.sub.3-c Y.sub.c (I)

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atom(s) perradical and a monovalent substituted hydrocarbon radical having from 1to 18 carbon atom(s) per radical, c is 0 or 1, n is 0 or an integer offrom 1 to 1000, m is an integer of from 1 to 500 and Y is a radical ofthe formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I)

with the proviso that at least one Y radical is present per molecule, inwhich A is selected from the group consisting of --O--,--S--, and##STR13## R² is selected from the group consisting of an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radical, R³ isselected from the group consisting of an alkylene radical having from 2to 4 carbon atoms per radical and an alkylene radical having from 2 to 4carbon atoms per radical which is substituted with a group selected fromthe group consisting of a hydroxyl group, methoxy group, ethoxy groupand a trimethylsiloxy group, R⁴ is selected from the group consisting ofa hydrogen atom and an alkyl radical having from 1 to 4 carbon atom(s)per radical and z is 0, 1 or
 2. 9. A composition containing theorganosilicon compound of claim 8 which crosslinks on exposure to lighthaving a wave length of from 200 to 600 nm.
 10. Th organosiliconcompound of claim 1, wherien Y is a radical of the formula

    --(CH.sub.2).sub.3 --O--CH═CH--CH.sub.2.


11. The organosilicon compound of claim 1, wherein Y is a radical of theformula

    --(CH.sub.2).sub.3 --)--CH.sub.2 --CH.sub.2 --O--CH═CH--CH.sub.3.


12. The organosilicon compound of claim 1, wherein Y is a radical of theformula

    --(CH.sub.2).sub.3 --O--CH═CH--CH.sub.2 --CH.sub.3.


13. An organosilicon compound comprising units of the general formula##EQU3## valent, hydrocarbon radical having from 1 to 8 carbon atom(s)per radical, which is interrupted by an ether oxygen atom, and Y is aradical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH═CH--CH.sub.2 --R.sup.4                                                 (I)

in which A is selected from the group consisting of --O--, --S-- and##STR14## R² is selected from the group consisting of an an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radical, R³ isselected from the group consisting of an alkylene radical having from 2to 4 carbon atoms per radical, and an alkylene radical having from 2 to4 carbon atoms per radical which is substituted with a group selectedfrom the group consisting of a hydroxyl group, methoxy group, ethoxygroup and a trimethylsiloxy group, R⁴ is selected from the groupconsisting of a hydrogen atom and an alkyl radical having from 1 to 4carbon atom(s) per radical and a is 0, 1, 2 or 3, b is 0, 1, 2 or 3, cis 0 or 1, the sum of a+b+c is ≦4 and z is 0, 1 or 2, with the provisothat the organisilicon compound contains at least oen Si-=bonded Yradical per molecule, said organosilicon compound is obtained byreacting in a 1st step, an organic compound (1) of the formula

    H.sub.2 C═CH--R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═CH--R.sup.4

in which A, R², R³, R⁴ and z are the same, with an organosiliconcompound (2) having at least one Si-bonded hydrogen atom in its moleculein the presence of a catalyst (3) which promotes the addition ofSi-bonded hydrogen to the aliphatic double bond, to form anorganosilicon compound having at least one Si-bonded Y¹ radical of theformula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═Ch--R.sup.4                                      (II),

in which A, R², R³ R⁴ and Z are the same as above, and then in a 2ndstep shifting the double bond in the Y¹ radical to the carbon atomadjacent to the ether oxygen atom by heating the organosilicon compoundobtained in the 1st step and having at least one Si-bonded Y¹ radical,in the presence of a catalyst (4), which promotes the rearrangement ofthe double bond.
 14. The organosilicon compound III of claim 13, whereinthe organosilicon compound (2) is a silane (2a) of the formula

    R.sub.d HSiX.sub.3-d,

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atom(s) anda monovalent substituted hydrocarbon radical having from 1 to 18 carbonatoms(s) per radical, X is selected from the group consisting of ahalogen atom and a radical of the formula--OR¹, in which R¹ is selectedfrom the group consisting of a monovalent hydrocarbon radical havingfrom 1 to 8 carbon atoms(s) per radical and a monovalent hydrocarbonradical having from 1 to 8 carbon atom(s) per radical which isinterrupted by an ether oxygen atom and d is 0, 1 or
 2. 15. Theorganosilicon compound III of claim 13, wherein the organosiliconcompound (2) is an organopolysiloxane (2b) of the formula

    H.sub.c R.sub.3-c SiO(SiR.sub.2 O).sub.o (SiRHO).sub.p SiR.sub.3-c H.sub.c,

in which R is selected from the group consisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atom(s) anda monovalent substituted hydrocarbon radical having from 1 to 18 carbonatom(s) per radical, c is 0 or 1, o is 0 or an integer of from 1 to1000, and p is 0 or an integer of from 1 to 500 with the proviso thatthe organosilicon compound (2) have at least one Si-bonded hydrogenatom.
 16. The organosilicon compound III of claim 13, wherein theorganic compound (1) of the formula

    H.sub.2 C═CH--R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 ═Ch--R.sup.4

in which A is selected from the group consisting of of --O--, --S--- and##STR15## R² is selected form the group consisting of an alkyleneradical having from 1 to 7 carbon atoms(s) per radical and acycloalkylene radical having from 5 to 7 carbon atoms per radical, R³ isselected from the group consisting of an alkylene radical having from 2to 4 carbon atoms per radical and an alkylene radical having from 2 to 4carbon atoms per radical which is substituted with a group selected formthe group consisting of a hydroxyl group, methoxy group, ethoxy groupand a trimethylsiloxy group, R⁴ is selected form the group consisting ofa hydrogen atom and an alkyl radical having from 1 to 4 carbon atom(s)per radical and z is 0,1 or 2 is reacted with a silane (2a) having anSi-bonded hydrogen atom of the formula

    R.sub.d HSiX.sub.3-d,

in which R is selected from the grou pconsisting of a monovalentunsubstituted hydrocarbon radical having from 1 to 18 carbon atoms and amonovalent substituted hydrocarbon radical having from 1 to 18 carbonatoms(s) per radical, X is selected from the group consisting of ahalogen atom and a radical of the formula --OR¹, in which R¹ is selectedfrom the group consisting of a monovalent hydrocarbon radical havingfrom 1 to 8 carbon atom(s) per radical and a monovalent hydrocarbonradical having from 1 to 8 carbon atom(s) per radical which isinterrupted by an ether oxygen atom and d is 0,1 or 2, in the presenceof a catalyst (3) which promotes the addition of Si- bonded hydrogen tothe aliphatic double bond, to form a silane having an Si-bonded Y¹radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z --O--CH.sub.2 --CH═Ch--R.sup.4                                      (II),

in which R², R³, R⁴, A and z are the same as above, converting thesilane having an Si-bonded Y¹ radical to an organopolysiloxane byreacting the silane with chloro- or alkoxysilanes and/or condensableorganopolysiloxanes to form an organopolysiloxane having at least oneSi-bonded Y¹ radical of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--R.sup.3).sub.z ----CH.sub.2 --CH═CH--R.sup.4                                      (II),

in which R², R³, R⁴, A and z are the same as above, and then in a 2ndstep shifting the double bond of the Y¹ group of the organopolysiloxaneto the carbon atom adjacent to the ether oxygen atom by heating theorganopolysiloxane obtained in the 1st step and having at least one Y¹radical, in the presence of a catalyst (4) which promotes therearrangement of the double bond to form an organopolysiloxane having atleast one Si-bonded Y group of the formula

    --(CH.sub.2).sub.2 --R.sup.2 --(A--.sup.3).sub.z --O--CH═CH.sub.2 --R.sup.4                                                 (I)

in which R², R³, R⁴, A and z are the same as above.
 17. A compositioncontaining the organosilicon compound III of cliam 16, which crosslinkson exposure to light having a wave length of from 200 to 600 nm.
 18. Acomposition containing the organosilicon compound III of cliam 13, whichcrosslinks on exposure to light having a wave length of from 200 to 600nm.